Ethanol → N-(6-(4-Aminophenoxy)pyrimidin-4-yl)phenylamine

HRID 1433649Notes

Reaction equation

HRID 1433649 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].C(O)C.O>C(OCC)(=O)C.CCCCCC.[Fe]>[NH2:1][C:4]1[CH:23]=[CH:22][C:7]([O:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 22936302N-(6-(4-Nitrophenoxy)pyrimidin-4-yl)phenylamine

Product 1

HCID 22936405N-(6-(4-Aminophenoxy)pyrimidin-4-yl)phenylamineYield 84.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

After suspending N-(6-(4-nitrophenoxy)pyrimidin-4-yl)phenylamine (508 mg, 1.65 mmol), iron powder (461 mg, 8.25 mmol) and ammonium chloride (882 mg, 16.5 mmol) in an ethanol (16 ml)-water (4 ml) mixed solvent, the suspension was heated and stirred at 80° C. for 20 minutes. Upon completion of the reaction, the reaction mixture was filtered with celite and washed in ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was suspended in ethyl acetate, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and then blow-dried: to obtain the title compound (387 mg, 1.39 mmol, 84%) as colorless crystals.

Workup

  1. additionmixed solvent
  2. temperaturethe suspension was heated
  3. customUpon completion of the reaction
  4. filtrationthe reaction mixture was filtered with celite
  5. washwashed in ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationthe drying agent was filtered off
  9. distillationthe filtrate was distilled off under reduced pressure
  10. customThe obtained crude product
  11. filtrationthe crystals were filtered out
  12. washwashed with hexane
  13. customblow-dried

Sources & evidence

ORD record
ord-51ec4697edf249a491eceda5986afd92
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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